Diethyl Ether → 4-[N-(benzylidene)aminomethyl]-1-(2-pyridinesulphonyl)piperidine

HRID 369067

Reaktionsgleichung

Reaktionsgleichung von HRID 369067
C(N(CC)CC)C.[CH:8](=[N:15][CH2:16][CH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[N:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[S:29](Cl)(=[O:31])=[O:30].C(OCC)C>ClCCl>[CH:8](=[N:15][CH2:16][CH:17]1[CH2:18][CH2:19][N:20]([S:29]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][N:23]=2)(=[O:31])=[O:30])[CH2:21][CH2:22]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Komponenten

6

Edukt 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 3787675Pyridine-2-sulfonyl ChlorideHCID 11820173N-Benzylidene(piperidin-4-yl)methanamine

Produkt 1

HCID 232848884-[N-(benzylidene)aminomethyl]-1-(2-pyridinesulphonyl)piperidineAusbeute 68,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Triethylamine (6.3 ml) was added to a cloudy solution of N-benzylidene-4-piperidylmethylamine (4.05 g) and pyridine-2-sulphonyl chloride (4.0 g) in dichloromethane (100 ml) and the resulting clear yellow solution was stirred for 14 hours. Removal of the solvent under reduced pressure gave a yellow solid which on addition of diethyl ether (100 ml) partly dissolved. The insoluble white solid (triethylamine hydrochloride) was removed by filtration. Evaporation of the filtrate afforded a flocculent yellow solid which recrystallised from ethanol to give 4-[N-(benzylidene)aminomethyl]-1-(2-pyridinesulphonyl)piperidine as a white crystalline solid (4.7 g).

Aufarbeitung

  1. customRemoval of the solvent under reduced pressure
  2. customgave a yellow solid which
  3. dissolutionpartly dissolved
  4. customThe insoluble white solid (triethylamine hydrochloride) was removed by filtration
  5. customEvaporation of the filtrate
  6. customafforded a flocculent yellow solid which
  7. customrecrystallised from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-af024818ab744dabafd169752ca52401
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06136825

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